


Startin' With Me

by Hannah_Radiant



Series: One-Shots [1]
Category: Supernatural
Genre: Gen
Language: English
Status: Completed
Published: 2017-10-15
Updated: 2017-10-15
Packaged: 2019-01-17 20:52:35
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,638
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12373827
Author URL: https://archiveofourown.org/users/Hannah_Radiant/pseuds/Hannah_Radiant
Summary: Dean is alone in a hotel room when he hears a song on the radio; instead of changing the station he listens. While listens he realizes it hits close to home.





	1. Startin' With Me

**Author's Note:**

> This is was a ONE-SHOT Songfic, but there was a request for a sequel so that will be the next chapter.

Dean was sitting alone in the hotel room again. It had been another long day. Since his return from hell things were different. Sam wasn't around much he was off doing his own thing, hunting on his own, even spending more time with that demon bitch Ruby. Out of sheer boredom he turned the radio on. Jake Owen's song Startin' With Me began to play in the background.

Dean considered changing it to a rock station but stopped when he realized it was hitting close to home.

_I had a one night stand with my best friend's baby sister  
And to this day he still won't speak to me_

He remembered his old friend Jason West from when he was 17. He ended up having a one night stand with his little sister; Emily. To this day Jason refused to talk to Dean. And Emily hated him as well. She never talked to him after that night when she found out she was nothing more than a one night stand. If only he could apologize for that one.

_I pawned my grandpa's old guitar in college  
For a case of beer and a tank of gasoline_

He ended up pawning an old guitar that belonged to his dad's father shortly after Sam left for college. Now that he thought about it he probably shouldn't of done that. He remembered his dad yelling at him for being so irresponsible and saying he shouldn't of sold that guitar. But at the time he didn't even care.

_I took a swing at my old man one Christmas  
I never dreamed that it would be his last_

Dean took a deep breath at that one. He did take a swing at his dad at Christmas. The only time he ever did and it was for some stupid reason. To be honest Dean didn't even remember what he swung at him for. But a few months later he sold his soul to let him live. Dean couldn't believe his father would do that even after what he did.

 _I wish mom had rung my neck_  
When she caught me with those cigarettes  
Which reminds me, I'm down to my last pack

Dean thought about his mom. Maybe it wasn't his mom who found him smoking but he did get caught. Bobby found him smoking a few weeks ago. He didn't even know why he started or why maybe it was because of the stress he didn't even care at this point. But it was something he normally did when Sam was gone. And as if on cue he lit up a cigarette with a sigh. He hated the fact he was a smoker now. He wished he could quit but it wasn't easy.

 _If I had a dime_  
_For half the things I did_  
_That didn't make no sense at all_  
_I'd be living a little higher on the hog_  
_If only I'd have known_  
_That later on down the road_  
_I'd look back and not like what I see_  
_I'd have changed a lot of things_  
_Startin' with me_

God there were plenty of things Dean wanted to change about himself. And come to think of it if he did have a dime for half the things he could probably upgrade this damn hotel room. He gave a weak laugh as the cigarette balanced gracefully on his lips glaring at the crack in the ceiling. Yeah he could go for an upgrade for once in his life. He deserved it didn't he? He saved lives but the only thanks he got was a night in jail because of fucking Shape shifters.

_I called my brother everything I could think of  
The night he wouldn't bail me out of jail_

There was that one time Sam actually refused to get Dean out of jail, it was shortly after he left for college. Dean had gotten into a bar fight and didn't want to call his dad. So he called Sam who told him to deal with it for once. He was furious this was one more to the list of why Sam should get smacked upside the head; right under leaving the family to go to school.

_I lost a job most folks 'round here would die for  
By laying out all night and raising hell_

He remembered having a job at a auto mechanic shop when he was 17 the one time he lived a normal life or did something normal. John took off hunting for a summer and Dean got a job. When summer was over he started up again. Dean could've kept his job but instead he decided to hunt with his dad and raise hell. Charming the girls and breaking rules; being a typical teenager. He was fired from his job but he didn't even care.

_And I let a woman that I love slip through my fingers  
Chalk another dumb move up to my foolish pride_

He thought about that one. He actually let  _two_  girls get away from him Cassie and Jo. Normally he wouldn't think about Jo but he realized he had a chance with her but blew it when he left before anything happened. And Cassie…god with Cassie he chose hunting over her. How could he do that? If only she could've met him half way…but then again he understood.

 _I wasn't there standin' by the bed_  
_When the preacher bowed his head_  
_With the family, the day my grandma died_

He remembered when his dad's mom died. Sam had kept calling trying to get a hold of him but Dean kept ignoring his calls. Even though his grandma was asking to see him one last time.

 _If I had a dime_  
_For half the things I did_  
_That didn't make no sense at all_  
_I'd be living a little higher on the hog_

He took another drag on his cigarette before putting it out. Time for that damn gum, the one to help him quit. Taking out a piece of the minty gum he began to chew it as if his life depended on it. Strangely in a way it kind of did.

 _If only I'd have known_  
_That later on down the road_  
_I'd look back and not like what I see_  
_I'd have changed a lot of things_  
_Startin' with me_

If he had known what he did then, maybe he would've never gone to hell. Maybe his dad would still be alive. Sam would still be there instead of being a rouge hunter with that bitch Ruby. He might not of been able to save his mom but maybe he could've saved others. So many others could've been saved.

 _If only I'd have known_  
_That later on down the road_  
_I'd look back and not like what I see_  
_Whoa, I'd have changed a lot of things_  
_Startin' with me_  
_Startin' with me_

Just as the last line of the song ended Sam walked in tossing his jacket on the chair and collapsing into the bed next to Dean. Not even a word was spoken like always. It was times like these that annoyed Dean the most.


	2. Sorry

**Summary for the Chapter:**

> Dean decides its time to make up for his mistakes. And fate has a funny way of making itself known.

**Notes for the Chapter:**

> Wow I've come a long way from when I originally posted this back in 2009. I'm not exactly thrilled with my writing for this one but I am slowly transferring all of my works from Fanfiction.net to here so oh well it is what it is.

Dean sat alone in the motel room again. This one seemed to be stuck in the 60s. Everything had a 60s mod look, as if Austin Powers himself decorated. How could Dean  _not_  laugh at it?

He felt his fingers twitch looking on the dresser across the room that had his cigarettes, God how he wanted one. But after Sam found out he rushed out to a grocery store and bought what could be 20 years worth of the patch and gum. Making Dean roll his eyes, the gum tasted like shit and the patch made him itch. Scratching the spot where the patch was much like he did when he was infected with the ghost virus.

"Damn patch…" he muttered to himself. Just as he began to scratch Sam walked into the room.

"Dean, stop scratching that. Let it do its job already. Speaking of jobs did you find us a new one yet?" he asked taking a seat on the bed next to Dean's.

"Y-No. Sam I never said s-s-sorry." He said it was hard for him to admit defeat. He was a Winchester for heaven's sake.

"I know. You don't need to. Just find us a job and Dean? If you don't stop scratching that patch I'm going to shove the gum down your throat." Sam said with an unusually pleasant yet creepy smile.

Nearly eight hours later they were in a small town in Pennsylvania. Parking in front of a motel Dean let out a sigh followed by a yawn.

"Sam. Sam wake up we're here." He said before getting out of the car.

Now that he was in the room he was stir crazy. After spending nearly eight hours sitting he had to move around. Grabbing his coat he walked outside looking around. He noticed a sign for an Air Show and gave a weak laugh.

"Yeah right." He said shaking his head before hearing a horn beep he turned to see an old jeep and a guy dressed like he was from the 1940s. Just then a beautiful blonde girl ran outside of one of the motel rooms. She was wearing a vintage dress but she was still gorgeous. She looked oddly familiar too.

"Emmy! Let's go we'll be late!" the man in the driver's seat called out. Dean just stared at the girl as she climbed into the vintage jeep. He still couldn't place it but he knew he had seen her before.

After driving to the air show he got out and looked around. Everyone seemed to be in vintage clothes. He noticed the sign that said 'WWII Weekend' it made sense now. Paying the entrance fee and getting his hand stamped he walked through the entrance. Looking around he saw planes from WWII and pretty much everything else you could imagine. He had to admit it was pretty interesting. Walking on the run way he passed multiple planes until he got to a building that actually had air conditioning. Inside he saw some veterans that were talking about there experiences and even some giving autographs. The sign at the back of the line said 'meet the real band of brothers'. Dean just shrugged and continued walking inside the building. Not looking where he was going he bumped into a girl.

"Sorry I wasn't looking where I was going." He said before noticing it was the girl from earlier.

"It's okay I wasn't either. Fascinating isn't it? All these planes and stuff? From the looks of it this is your first time at the air show. I'm Emily West and you are?" It hit Dean like a semi truck and he just stared at her. That's how he knew her! It was Emily West his ex best friend's kid sister!

"Uh…James Hetfield." He said with a smirk hopefully she wouldn't catch on to the name or recognize him.

"James Hetfield? Isn't he the lead singer of that band Metallica?" she asked with a raised eyebrow, all Dean could think of was;  _shit she knows about Metallica._

"You know Metallica?" He asked a little impressed she knew the lead singer's name considering the only non-pop or country stuff she listened to was the Beatles and some of Aerosmith when he knew her way back when.

"My older brother Jason listens to them occasionally. So what's your real name?" she asked with a grin. It was the grin that made him want her all those years ago.

"You won't like to hear it. Trust me on this one." He said with a weak laugh.

"Oh; really now? Try me." she said crossing her arms as she raised an eyebrow again.

"Dean Winchester." Right when he said his name he watched as recognition met her eyes and in the background a mortar round being set off as a demonstration went off, making Dean himself, jump. She glared at him before punching him in the jaw catching him off guard, sending him staggering back a few steps as she stormed off. Dean rubbed his jaw in pain even though he knew he deserved it he didn't think she'd punch him.

"Son you alright? What you do to the poor girl?" A veteran asked him Dean turned to look at the man who was holding a hand of a woman who had to be his wife.

"Probably what you did to me sixty years ago Richard. Now young man, you go apologize to her and if you're lucky she'll forgive you like I did Richard." The woman said with a smile before leading her husband away. Dean just stood there with his eye brows furrowed.

"Crazy old ladies…" he muttered before walking off in the direction Emily ran off. Seeing her looking at vintage sunglasses he gave a sigh. It was now or never, he was going to apologize.

"Emily? Can I talk to you for a sec?" Dean said hesitantly, Emily turned around with a glare on her face.

"Why should I talk to  _you_? After what you did to me? I don't think so  _Winchester_!" She screamed in anger.

"Look I wanted to apologize. Okay? I get it was an ass back then, I really mean it when I say I'm sorry. Look you don't have to talk to me ever again I just want you to know I mean it." He said with a sigh before turning away. Emily didn't say a word.

"Dean? How long have you been planning to say that?" she asked softly.

"Since the day it happened. Now I'll leave you alone…good bye Emily." He said once again walking away. What surprised Dean was Emily ran after him.

"Call me crazy but I accept your apology." She said with a half smile.

Months went by and Dean was still talking to Emily through e-mails and texting her. Sure he never mentioned what he did for a living, how would that turn out? He noticed one text that she sent him that morning, Bad Company began to play as his phone vibrated; signaling she text him again.

_**Hey just got ur text. I'm in New Orleans visiting my old roommate. Wish u were here lol** _

Dean felt himself grin getting texts from Emily seemed to be the highlights of his day. Things like this normally made him roll his eyes but now it seemed normal. And at this point Dean could care less what people thought of him. Right when he was about to respond Sam walked in with the newspaper.

"Dean we got a possible job opportunity in New Orleans. You interested?" he asked Dean smiled to himself quickly texting Emily back.

_**See you there babe. I have to go to New Orleans for work. ;)** _

After a two day, drive the brothers reached their hotel, it was an old one that had to have been there for nearly 60 years the paint was chipped on every single door and the windows were filthy. But it was cheap, cheap was good. Well sort of good.

Walking into the room Dean held back a frustrated groan. The room was an ugly puke green color and had moss colored carpeting but the beds looked alright for once. That is until Sam fell, face first into his making it collapse to the floor.

"Jeez Sammy you putting on weight?" Dean said with a smirk only to have a pillow which had to of had rocks in it hit him.

"Can we find a different motel Dean? The bed smells like a toilet…" Sam said as he stood up.

"Sure thing Sammy but where are we going to stay?" Right as Dean said that his phone went off.

**_Vanessa said you two should stay here. She's got a huge house here. You each could get your own room. ;)_ **

Dean looked at Sam with a smirk, before holding his phone up.

"Found a place. Let's get out of this place." Throwing the room keys to Sam he loaded their stuff back into the impala and hopped in the driver's seat just as Sam got in the passenger seat.

"Where are we staying?" Sam asked raising an eyebrow. After Dean told him Sam was a little curious. It was extremely rare that they got to stay in a house, the only times they got to was when they stayed at Bobby's.

Dean grinned as he saw Emily leaning against one of the giant pillars on the porch. He felt his heart actually skip a beat. She wore a gorgeous yellow sundress with flowers on it. Her long curls hung loosely around her rosy cheeks and her lips had a light gloss, knowing her it was strawberry flavored, she loved strawberry lip gloss. Which he had no problem with; it made kissing her even better. After that thought Dean paused, he was falling hard for her and at this point he didn't even care.

"Dean, I was wondering when you'd show. Took you long enough." She said with that grin of hers never missing a beat he gave her the smirk that he knew made her knees go weak.

"Sorry babe didn't know I was supposed to hurry." He said grinning this time.

That night Dean sat in the king size bed in his room; for once he had his own room. Sam was across the hall already sound, asleep. Looking at his cell phone; reading the time 11:48 pm. For some reason he just couldn't sleep. He turned to look at the door when he heard a soft knock. Waiting for the person to open the door, he grinned when he saw it was Emily. She was wearing a Led Zeppelin shirt that stopped at her mid thigh.

"Zeppelin rules…" he said with a smirk making her giggle before trying to pull the shirt down to cover more.

"I couldn't sleep…and wanted to see if you were asleep." She whispered gracefully gliding over after she shut the door. He pulled her closer to him making her stand between his legs. Her hands rested on his bare knees as she bit her lip. Pulling her in for a kiss he smiled.

"I'm awake. Wide awake…" he trailed off raising his eyebrows.

Less than five minutes later both had practically ripped the other's clothes off and were kissing the other as if it was a necessity to live. He trailed his hands from her cheeks to her waist, going lower making he moan.

"Emily…I'm sorry…for last time. I was an ass." He said as he kissed her. In the background he could faintly hear the radio he left on to help him sleep. It was playing some band that Sam would occasionally listen to, Buck Strawberry or something like that. Dean didn't care.

"Ohh nice! I love Buck Cherry…I swear it's like radios can read your mind! They always play the right songs…" Emily said with a grin, Dean gave a chuckle as he kissed her.

_Oh I had a lot to say_   
_Was thinking on my time away_   
_I missed you and things weren't the same_   
_'Cause everything inside it never comes out right_   
_And when I see you cry it makes me wanna die._

Dean deepened the kiss before thrusting into her making her gasp. He smiled again, mentally shaking his head as he realized how he had become a softie over the years. Before he was the 'wham-bam-thank **-** you **-** ma'am' kind of guy, but with Emily he was willing to actually be  _more._

_I'm sorry I'm bad, I'm sorry you're blue_   
_I'm sorry 'bout all the things I said to you_   
_And I know I can't take it back_   
_I love how you kiss, I love all of your sounds_   
_And baby the way you make my world go 'round_   
_And I just wanted to say I'm sorry._

Dean watched Emily's face as he quickened his pace. Her delicate hands latched onto his short locks, pulling his face closer to kiss him again. Her legs wrapped around his waist pulling him closer. Never before had Dean felt this good. It was far better than any woman he had been with. Cassie was like an armature, he was even forgetting about the bendy-ist week of his life! Wait was it even a week? He couldn't even think straight anymore!

_This time I think I'm to blame_   
_It's harder to get through the days_   
_We get older and blame turns to shame_   
_'Cause everything inside it never comes out right_   
_And when I see you cry it makes me wanna die._

Hearing Emily's little gasps of pleasure was driving Dean over the edge. He flipped them over so she was on top. His eyes never left hers as he watched her keep the pace.

_I'm sorry I'm bad, I'm sorry you're blue_   
_I'm sorry 'bout all the things I said to you_   
_And I know I can't take it back_   
_I love how you kiss, I love all your sounds_   
_And baby the way you make my world go 'round_   
_And I just wanted to say I'm sorry._

Dean was nearing his climax but he knew he had to wait for Emily. As if on cue she came with a scream Dean came seconds later. But neither stopped their thrusts. She flipped them over so he was on top of her again. She was kissing him frantically as if he was her life line.

_Every single day I think about how we came all this way_   
_The sleepless nights and the tears you cried_   
_It's never too late to make it right_   
_Oh yeah_   
_Sorry!_

He felt her coming close to another climax this time he came at the same time. Both were panting madly. But the two refused to stop. It was as if they were on auto pilot. Neither knew how much they needed each other.

_I'm sorry I'm bad, I'm sorry you're blue_   
_I'm sorry 'bout all the things I said to you_   
_And I know I can't take it back_   
_I love how you kiss, I love all your sounds_   
_And baby the way you make my world go 'round_   
_And I just wanted to say I'm sorry._

"D-D-Deannn!" she gasped as her arms wrapped around his neck. He began to slow his pace. This time he was going to do this right. He was going to show her she was different than the usual 'wham-bam-thank **-** you **-** ma'am'. He was going to make love to her _._  He couldn't imagine that he  _Dean Michael Winchester_  was going to be willing to  _make love._  He was willing to turn this into an actual relationship. He didn't even have that with Cassie.

_I'm sorry baby._   
_I'm sorry baby._   
_Yeah, I'm sorry._

Finally they both climaxed one more time before falling to the bed. He rested his head on her chest as he tried to catch his breath.

"Call me crazy…but I think I love you Dean…" she whispered softly, making Dean look up with a smile.

"I think I might be becoming a softie but I think I might love you too…" he said with a shrug.

"Ever, the romantic Dean." She said with a laugh before something slammed against the door making her jump.

"What the hell was that?" Dean asked jolting out of bed.

"DEAN! WOULD YOU BE QUIET NEXT TIME?! I WAS SLEEPING! GOD NEXT TIME JUST GO TO A MOTEL!" Sam screamed making Dean and Emily laugh quietly.

"Oh god we woke Sam!" Emily said with a blush.

The next morning at breakfast Dean was sneaking glances at Emily who just smiled and blushed.

"So Sam you threw a shoe at my door last night. What gives?" Dean said with a smirk.

"God Dean you were so damn loud I think they heard you in Sydney!" At this Emily's old roommate; bust out laughing.

"You're kidding me? I didn't hear a thing!" she said with a grin. Emily turned bright red as her friend looked at her.

"Sorry…I didn't know we were that loud…" she whispered in embarrassment.

It had been two years since that night. And Dean was practically in shock. He was actually going through with this.

"Dean you going to be alright?" Sam asked in a whisper. Dean looked to the crowd friends and practically family, were sitting in the fold out chairs. The music cued and Dean looked up. There she was in a tea-length dress in lightweight v-neck straps in front and back. Beaded empire waist is adorned by a delicate bow at center front. He only knew the details because of how she described it. She was breath taking; Jason was walking her down the isle. He couldn't believe it, He was getting  _married_! His mind seemed to blank out until he heard the preacher's words.

"Do you Dean Michael Winchester take Emily Nicole West to be your wife?" Dean snapped out of his trance and looked at the preacher then looked at Emily.

"I do." He said with a grin.

"Do you Emily Nicole West, take Dean Michael Winchester as your husband?" the preacher asked.

"I do." She said with a grin. Dean looked at his new wife with a grin. Only just hearing the preacher say he could kiss his bride. Dipping her low he kissed her passionately chuckling at her squeak in shock and the cheers of the guests.

When it came time for the dance Dean grinned. It was Bad Company; 'Ready For Love'. He was thrilled that she agreed to let them dance to that. Only if she chose the second dance; she chose a country song. Dean was hesitant at first until he saw how much it meant to her. She chose 'Livin' Our Love Song' by Jason Michael Carroll. It was an upbeat tune and he was actually okay with the choice; though he swore never to mention that to anyone.

Twelve years went by and Dean couldn't believe it time sure flies. He was watching his little princess concentrate before shooting her bb gun. Her mother and baby brothers were out visiting their Aunt Vanessa. Dean said he would watch Samantha, their oldest daughter who was named after her uncle and her godmother. Samantha Jo Winchester was a complete daddy's girl. She had her father wrapped around her little finger. He only looked up when he heard the pop of the bb gun and the shatter of glass.

"DADDY! I DID IT!" she said with a grin. Dean smiled as he noticed his little girl was a pro when it came to shooting a gun. But he had failed to mention that to his wife about his little girl using a gun.

"Dean you know Emily will have your ass if she knew Sammy was shooting yet alone holding a gun?" Sam said as he walked over holding his youngest son. Sam had married Ruby and surprisingly had children with her.

"Yeah well what she doesn't' know…" he said before hearing someone clear, their throat behind him.

"DEAN MICHAEL WINCHESTER! I thought I told you she isn't allowed to even  _hold_ a gun! AT LEAST NOT UNTIL SHE IS 18!" Emily yelled her hands on her hips.

"But mom what if a werewolf attacks? Or a ghost comes and tries to hurt us?" Sammy said giving her mother the puppy dog pout.

"God, why did you have to get your father's eyes? Fine you can use a bb gun THAT'S IT. And what makes you think that  _I_  can't defend you? You aren't the only one your father taught to shoot." She said with a smirk before kissing her husband.

**THE END**


End file.
